


Of Old Dogs and New Tricks

by Udunie



Series: Tricky [1]
Category: Original Work
Genre: Anal Fingering, First Time, M/M, Prostate Massage, Vibrators
Language: English
Status: Completed
Published: 2016-02-06
Updated: 2016-02-06
Packaged: 2018-05-18 14:01:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,410
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5931006
Author URL: https://archiveofourown.org/users/Udunie/pseuds/Udunie
Summary: <blockquote class="userstuff">
              <p>If there was one thing Troy knew, it was that he was in no way, shape or form a twink.</p><p>Sure, he was on the leaner side, but he was tall with wide shoulders and big hands - among other things. He was also getting into the age when his partners wanted to call him Daddy. He had no problem with that, he was always a top, there was nothing bad about that.</p><p>But… Sometimes he couldn’t help wondering what it might feel like to be on the receiving end of things, to be in a more submissive role.</p><p>It was mostly wishful thinking anyway. It wasn’t like he was a hermit, or anything; he was still good looking, even though his hair was going gray and he needed to wear glasses for driving. He had a lot of sex. Good sex, even. It wasn’t anybody’s fault that it was getting kind of… boring.</p>
            </blockquote>





	Of Old Dogs and New Tricks

**Author's Note:**

> Hello, lovelies!
> 
> This is another one for my lovely friend Elina, who gave me a lovely little prompt!
> 
> Once again, than you to Emma for being patient with me!

**** If there was one thing Troy knew, it was that he was in no way, shape or form a twink.

Sure, he was on the leaner side, but he was tall with wide shoulders and big hands - among other things. He was also getting into the age when his partners wanted to call him Daddy. He had no problem with that, he was always a top, there was nothing bad about that.

But… Sometimes he couldn’t help wondering what it might feel like to be on the receiving end of things, to be in a more submissive role.

It was mostly wishful thinking anyway. It wasn’t like he was a hermit, or anything; he was still good looking, even though his hair was going gray and he needed to wear glasses for driving. He had a lot of sex. Good sex, even. It wasn’t anybody’s fault that it was getting kind of… boring.

  


***

  


Troy was getting a drink in the Princess - the place he usually went to pick someone up on Saturday nights. He wasn’t a predator, or something, he just had a hard time finding someone to stick around. The kind of guys that found him attractive (usually more than ten years younger than he was) weren’t looking for anything lasting. He tried telling himself that he was okay with that, that having a string of one-night-stands was enough, that he was just getting old and sentimental.

It didn’t really help.

He was kind of dejected. Yesterday had been his fortieth birthday and all he got was a text from his sister and four separate dickpicks from previous hookups who cared to find out when he celebrated the big day.

Lou, the bartender put a pink cocktail in front of him, making Troy raise an eyebrow. He wasn’t really a cocktail guy.

“Don’t look at me like that, T, it’s from the guy over there,” the man said with a shrug, pointing a finger down the counter.

Troy followed his motion, seeing a rather good looking man sitting at the end of the bar. He was on the short side, blond and blue eyed, but built. He was exactly the kind of guy Troy usually went home with, except that Troy knew that he was not. He’d seen him before and they had the same taste in partners - well, it wasn’t really a taste thing as far as Troy was considered, but whatever. The guy was a top, or maybe actually one of those doms young twinks fantasized about… His name was Eric, if he recalled correctly.

He felt a bit wrongfooted, not really getting what was happening. There was no way Eric was hitting on him. Not only was it Troy that had to do the wooing most of the time, but he was pretty sure the man knew that he… well, he just wasn’t the type who got drinks bought for him.

_ Can I join you?  _ Eric mouthed at him over the noise of the busy bar. Troy nodded at him uncertainly, he didn’t have a reason to say no, and didn’t want to be rude.

He was almost a head shorter than Troy himself, but the man made his way through the crowd with the confidence of a giant. It was kind of fascinating.

Troy didn’t want to stare, so he turned away, eying the cocktail distrustfully. He wondered sometimes how these things tasted, but it was alarmingly pink. With a cherry on top.

“Hey,” Eric greeted as he sat down on the free stool beside him, his body turned towards Troy, legs open comfortably. He had no idea why he was noticing these things, he wasn’t really observant, usually.

“Um, hi. Thanks for the drink,” Troy told him, nodding towards the martini glass.

Eric grinned, face lighting up.

“It seems like you’re not a fan of the Baby Martini I chose.” 

He didn’t sound accusing, just happy to be having a conversation with him. Troy didn’t know what to think. The whole situation was a bit surreal, he wasn’t used to being treated to things.

“It’s not my usual,” he admitted somewhat sheepishly. “Not like there’s anything wrong with it, I mean…”

“Well,” Eric said with a wink, “maybe you should give it a try? I think it will be way better than you think.”

Troy opened his mouth and then closed it. Why the hell not? He was forty now, and he wasn’t one of the macho assholes who thought a lick of pink would destroy their masculinity.

He nodded, picking up the drink and taking a sip.

It was shockingly strong. And sweet. It was delicious, actually.

“It’s surprisingly nice,” he said, giving Eric a smile. Maybe it was the alcohol. The man chuckled.

“See, I told you! It doesn’t hurt to try new things once in awhile…” he said, still grinning. Troy had the strange feeling that he wasn’t even talking about the drink anymore.

Eric waved the bartender over and got himself a beer.

“So, what are you doing today?” he asked, taking a gulp. Troy sipped his Baby Martini, not knowing how to answer. He was there to pick up someone for a night, but that seemed like the wrong thing to say. “I mean, now that I ruined your chances at getting laid,” Eric finished cheekily.

Well. Troy wasn’t sure where this whole thing was going. He didn’t know…  _ Usually  _ he would spot a twink, invite him to a drink, chat a bit and ask if he wanted to come over. Then he would fuck the guy and move on when he woke up alone in the morning. 

This situation was getting out of hand, he didn’t think Eric was interested in anything he could offer, but then why the whole charade?

“Um… I could still do that?” Troy asked uncertainly. Maybe Eric wanted to get fucked? He could be a switch, even though his reputation said otherwise. Probably.

The man laughed. It was a nice sound, not mean at all, just really cheerful. Troy liked it, Eric was a charming guy.

“Maybe,” he said, watching as Troy finished off his cocktail. His eyes were intense, tracing his lips and making him blush. Shit, he didn’t remember the last time someone got him so flustered.

“Or maybe you could come up to my place and continue the rest of the night in the spirit of trying out new things.”

Troy coughed, the alcohol burning his throat when he swallowed the last sip wrong. Was Eric saying what he thought he was? Was he making fun of him or something?

The man must have seen what he was thinking in his eyes, because he dropped a casual hand on Troy’s knee, looking earnest as he spoke.

“It’s just an offer, though. I can’t put my finger on it, but you look like you could use a bit of fun… And, I have to admit, I’ve been meaning to ask you out for a while now.”

Troy had no idea what to say to that. He didn’t despise bottoming, he was kind of curious, but everybody always expected him to top. He never. He never actually did that before.

“I need another drink,” he said finally, part of him way too eager to just go with it.

Eric patted his knee and winked.

“You could get another one, but I would rather have you sober.”

Troy looked into his eyes for a second, searching for god knows what. This was probably the weirdest night of his life.

“Okay.”

  


***

  


Eric’s place was nice, in the better part of the city, actually not that far from Troy’s flat. It was minimalistic with a lot of white walls, dark wood and metal. 

Troy was also getting nervous. This was stupid. He tried to imagine getting fucked by the man, but his brain kept telling him that he was too big, too old, too… not twink. It was annoying, because he knew things didn’t work like that. There were a lot of hairy, muscular men out there who liked taking it in the ass, but he still felt so… inadequate.

“Hey,” Eric said, putting a hand to the small of his back and guiding him to the couch. “Sit down and relax, hm? I will get you a glass of water.”

Troy nodded, and did as he was told, feeling out of sorts. The man returned shortly with a tall glass of water that Troy drank down in one go. Nerves made him thirsty.

Eric plopped down beside him, close enough that their thighs were touching.

“Okay, what got you so tense? I’m not going to jump you, or anything,” he said, and there wasn’t a lick of impatience in his tone. It seemed like Troy was fed up with himself enough for the both of them. He put his glass down before speaking, deciding to get it off his chest, no matter how embarrassing it was.

“I just… I never bottomed before,” he admitted, feeling his face heat up.

Eric didn’t say anything for a long second, making Troy wish that he stayed silent, but then the man just forced out a long breath, taking his hand.

“That’s completely okay, I knew that you were topping usually, but I didn’t know you never did it before… We don’t have to do anything you don’t want.”

Troy pulled a face. It wasn’t that he didn’t want to, just…

Eric squeezed his fingers and it made some of the tension leak out of his muscles, just enough that he could look the man in the eyes.

“It’s not that I don’t want to, but… Well, it’s kind of really weird to be a… a virgin at my age,” he blurted out. God, this whole situation was so stupid, there was no way Eric would still want to have anything to do with him.

The other man surprised him again - for the upteenth time that night - and smiled, cupping Troy’s face with his free hand. 

“It’s all right, I will take good care of you, promise,” he said, leaning in slowly, giving Troy enough time to pull his head away if he wanted. He didn’t.

Eric’s lips were soft and warm and he was a very good kisser, not like Troy wasn’t one himself, but this was different. This time, he wasn’t expected to take the lead, in fact, there was little he could do when Eric’s tongue teased his lips open, licking along the seam for entry.

Troy shivered and just went with it, letting the man do what he wanted. And what he wanted was apparently to gently but thoroughly fuck Troy’s mouth in the most delicious way possible.

When they came up for air, he was actually dizzy, feeling a bit like the room was spinning around him. His cock was hard.

“That was lovely,” Eric said, looking a bit dazed himself, making Troy feel a bit better about getting so worked up from just a kiss. “What do you say we take this to the bedroom?”

Troy nodded, feeling a bit dumb with arousal. Yeah, yeah that was a good idea.

  


***

  


Eric’s bedroom was much like the rest of his place, simple and clean. He had a big, modern four poster bed that kind of looked like a box. Or a cage. It made Troy a bit nervous, but not necessarily in a bad way.

They kissed some more while they undressed, he had a feeling that Eric just wanted to distract him, so he wouldn’t feel so anxious about what they were about to do... Troy found that he loved how short Eric was, that he had to bend down for those nice, languid kisses, and at the same time not being expected to be in control of them.

“Well, look at you,” Eric said, clearly impressed as he looked at Troy’s naked body. Yeah, he had a pretty big cock. His partners were usually all over it, wanting to get it in them, but now it was different. Eric didn’t have anything to be ashamed about either, but he was still obviously smaller than him.

The man took Troy’s cock in hand, giving it a few slow strokes, making him moan. It felt good.

“You are a big boy, that’s for sure.” 

Troy swallowed. Maybe Eric changed his mind, and wanted to do it the other way around. As disappointed as the thought made him, it was still better than thinking about how his belly twisted with anticipation when Eric called him a  _ boy _ .

“Get on the bed, beautiful, let me get a few things,” the man told him, making Troy lift an eyebrow. Other than some lube and condoms - that he could see on the bed - he had no idea what they could need. Eric just grinned, getting on his tiptoes to get another kiss before nudging him towards the bed.

“Trust me, I want to make your first time something that you can’t forget.”

Troy nodded, licking his lips as he sat down on the edge of the mattress. He watched Eric walk into his closet, rummaging around for a minute before returning with a bunch of… sex toys.

He felt his face grow hot. He was kind of a vanilla guy, so yeah. It was a tiny bit intimidating.

Eric deposited everything on the bed and then climbed into Troy’s lap, kissing him long and dirty. It took his breath away and his hands instinctively found their way around the man’s waist.

“Hey, it’s fine. I told you I will take good care of you, hm? I want to blow your mind, big boy, okay?” Eric told him when they broke apart. 

He nodded, still feeling unsure a bit, but more turned on than he had been in a long time.

“Great. I need you to lay back… that’s it, that’s my good boy.’

Troy shivered. It should have been ridiculous; he was older and bigger than Eric, but there was something in the tone of his voice that had his spine melting.

He shuffled up the bed and Eric followed him, grabbing two pairs of handcuffs from his pile of toys. Troy wasn’t sure he… that he would like that.

The man straddled his belly when he lied back, leaning down to kiss the tip of his nose and making him go cross-eyed for a second.

“Do you know what a safeword is, big boy?” he asked.

Troy did, he wasn’t completely ignorant of these things, he just never tried them himself. He nodded, licking his lips.

“That’s great. I’m going to need you to chose one. You say it, and everything stops, okay?”

Of course, there was no guarantee that he would keep his word. There was little Troy could do if he was already tied up and at Eric’s mercy, but looking into those bright, blue eyes made him believe the man against all common sense.

“Brick?” he asked uncertainly, it was the first thing that came to mind.

Eric grinned, rubbing Troy’s chest with his palms, trying to work the tension out of his muscles.

“Brick is good. Okay, beautiful, remember that word, hm?”

He nodded again. He could do that. Probably.

“I’m going to tie you up a bit. Just say the word and you’re free…” Eric promised as he fixed first one, then his other wrist to the bedposts. The handcuffs were lined with something soft and not too tight, but they still filled Troy with a kind of nervous anticipation. He’d never been tied up before.

“Why?” he blurted out. He wasn’t… He wasn’t really against it, but he didn’t understand why they needed to do it this way. Eric cupped his face.

“Well, for one, you look beautiful all laid out for me,” he said, grinning when Troy blushed. “And I want you to only concentrate on what happening with you down there.”

He kissed him again and then scooted down along his body, planting himself between Troy’s parted legs. He ran his hands up and down his thighs without urgency. That was also kind of new. He couldn’t remember the last time he was with someone who savored things the way Eric seemed to do.

He kept petting him until Troy was as relaxed as he could be, and then pushed at his knees until his feet were planted firmly on the mattress. Eric smiled, picking up the lube and squirting some on his fingers.

Troy watched, swallowing thickly. He did that dozens of times, but still, looking at the man warming the lube for him was a completely different animal.

“No need to worry about anything, big boy. Close your eyes if it helps you relax, I will be slow and gentle.”

He did just that, feeling his nerves acting up again, weighting down the pit of his stomach. This was so stupid. He fucked a lot of people and they enjoyed it. He knew he would too, he hoped, but who knew? Maybe he was too old to try new stuff.

His body jerked when Eric touched his down there, fingers light and easy over his skin as they slid into his crack. The lube wasn’t cold, but it the feeling of it was still strange.

The man kept a hand on his thigh, massaging him all the while.

“That’s it, you’re doing wonderfully, big boy, so good for me.”

Troy shivered, barely able to keep a moan at bay. He didn’t know if it was the result of those skilled fingertips dancing around his entrance or Eric voice saying those things… Both, probably both.

The man kept talking to him, gentle and patient, even though Troy felt ridiculous for being so difficult about this. When finally Eric slid a finger into him, his whole body shuddered. It didn’t hurt a bit, not after he was so carefully coaxed open, but it was still an alien sensation.

“You feel so nice, beautiful, hot and soft around me… Wait until we find your button,” Eric told him, and Troy could hear he was smiling, maybe a little proud even. He didn’t know why that filled him with so much warmth.

He didn’t have much time to concentrate on that though, because Eric curled his finger and pushed the tip against a spot inside him that made his whole body light up with electric pleasure. Troy saw so many times as people withered on the sheets when he did the same, but could never quite understand it. Now he did, and it left him breathless.

He was panting, eyes staring at the ceiling, trying to calm his heart, but it was useless when Eric kept doing it again and again, making him see stars.

“F-fuck,” he moaned as his cock started to ooze precome all over his belly. It was hard to think. He wanted to jerk off, but he couldn’t, not with his hands tied.

“Yeah, that’s right, big boy. I’m going to make you come just like this, and then I’m going to fuck you when you’re all nice and loose for me,” Eric said.

Troy was trembling, feeling himself break out in a sweat. 

“What? No, I… I can’t…” He was pretty sure that was just a legend. And even if it wasn’t, there was no way he could come untouched.

“Yes you can, beautiful,” the man promised, adding a second finger. There was a bit of a burn at the stretch, but still no pain, just a quiet heat eating away at him from the inside.

He threw his head back into the pillows, eyes shut tight. Eric didn’t give him rest, he kept rubbing him there, fucking his hole slowly and scissoring his fingers on occasion.

Troy’s cock twitched again and again. He felt like he was just about to come, and at the same time like he could never reach it.

“Shh, it’s okay, you’re alright, you’re doing wonderfully, big boy, so very good…” Eric said. Troy didn’t even notice that he started making needy, desperate little sounds. “Going to add another finger, okay? Relax for me.”

It was a bit of a strain, but once the third finger was in there was a weight to things that wasn’t there before. It was strange and intense and absolutely amazing.

“That’s it, beautiful, going to make you come now.”

Troy shook his head, throwing it from side to side, too overwhelmed for words. He still didn’t think it was possible, even though he could feel the electric heat gathering under his navel. It didn’t feel like the usual buildup, it was more subtle, but somehow all encompassing.

Eric picked up speed, thrusting his fingers inside quick and easy, aiming for that spot over and over. The lube was making obscene sounds…

Troy was caught off guard when he came, it was… nothing he experienced before, the pleasure didn’t so much erupt from him, as it washed over his body in waves that kept crashing over his for what seemed like entier minutes.

He might have shouted, he wasn’t sure. He didn’t really care.

  


***

  


By the time his brain came back online, Eric was peppering kisses on his slack face, smiling like he won the lottery.

“There you are, there’s my big boy,” he said when Troy’s eyes finally managed to focus on him. He pulled on his hands but they were still tied up.

“Mn, not so fast, beautiful, we’re now finished yet,” the man told him, stroking down Troy’s chest as he pulled back. His skin broke out in goosebumps when the warmth of Eric disappeared from above him.

“What?” his voice sounded rough and tired… but sated most of all.

“Well, technically you still haven’t lost your virginity,” Eric said, giving him a wink. Troy blinked. Oh.

His back arched when he felt fingers breaching him again. He was a bit oversensitive, but there was no pain, his body too pliant to put up a fight. Eric pumped his digits a few times before they were gone, leaving Troy achingly empty. He had to bite his lips to stop himself from whining at the loss.

“It’s fine, I just want to make sure you are going to have the best sex of your life,” the man promised. He picked up one of the toys - an egg vibrator - lubing him up. Troy’s hole clenched and unclenched, feeling apprehensive and excited at the same time.

Eric was gentle but insistent as he pushed the toy inside. It wasn’t too big, sliding in easy, the wire of it hanging out and teasing his rim. He pushed it in as far as he could with his fingers, but didn’t try to aim for Troy’s prostate again.

“Almost there,” Eric said, opening the condom and rolling it onto his cock. Troy would have lied if he said he wasn’t still a bit nervous, but when the man finally breached him, dick sliding into his hole, stretching so… right, it felt like everything in his world finally clicking into place.

His cock was longer than his fingers had been, pressing the vibrator deeper into Troy, making him moan.

Eric stroked his hips, fingers careful as he waited for him to adjust. It didn’t take long.

“Ready, beautiful? Let’s see if you can come again, on my dick this time,” Eric whispered. He didn’t think that was possible, but the man picked up the remote of the toy and turned it on, making Troy’s whole body clench up in a delicious mix of shock and pleasure. He never felt anything like that before and it was shortcircuiting his nervous system.

Eric was talking to him, praise falling from his lips as naturally as breathing. Troy could barely catch the words, but they still managed to warm him from deep inside as the man finally started to move, fucking him slow and steady.

“Doing so good, big boy, so good for me, taking it so well…” 

A second ago, he hadn’t been sure he could come again tonight - he wasn’t a teenager anymore - but he wasn’t so certain anymore, not when Eric kept talking to him like, not when his cock felt like it belonged in his hole, hitting all the right spots.

The vibrator was a steady, maddening hum in him, turning his insides into liquid heat that pooled low in his belly.

It was becoming hard to think.

“Yeah, just like that, beautiful, just relax and let it happen, I’m going to take care of you…”

Troy was getting dizzy. His cock was aching, getting hard again too soon, too fast. He couldn’t understand what was happening to his body, but he couldn’t stop it either, wasn’t sure he wanted to.

It wasn’t enough though, not when he already came once. The aimless arousal was getting too intense, making him whine and moan in desperation, but Eric wasn’t letting him suffer.

“That’s okay, big boy, that’s completely fine, let me help you,” he said as he sped up his thrusts, the sound of skin slapping against skin loud in the room. He kept one hand firmly on Troy’s hip, the other gently taking hold of his oversensitive cock.

Even that light touch was enough to make him hiss and pleasure boil under his skin at the same time.

Eric started to jerk him off, fingers just the right kind of tight around Troy’s girth.

“Yeah, beautiful, just like that, come for me…”

Troy did. It almost hurt and it made his whole body size up, clenching down on Eric’s dick and making him bite off a groan. He was only dimly aware of the man’s hips stuttering forward and pressing into him a few more times and then stilling with a cry.

Eric fell forward, barely catching him on his arms before falling on Troy. They were both panting hard, sweat slick chests touching on the inhales.

“P… Please turn it off,” Troy pleaded, the low vibrations turning painful against his overused prostate. Eric obliged immediately, pulling out carefully from his hole and tying the condom off.

Troy was half asleep, exhausted and content beyond belief by the time he was released and cleaned up. The lights were turned off, and the next thing he knew was a warm body pressing against him, burrowing close.

He turned Eric around until he could spoon his from behind, bigger body enveloping the smaller man. It felt just right, fitting together.

  


_ _

**Author's Note:**

> You can find me at udunie.tumblr.com!
> 
> Comments are love :D


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